Hunsdiecker reaction

Hunsdiecker reaction

The Hunsdiecker reaction (also called the "Borodin reaction" after Alexander Borodin) is the organic reaction of silver salts of carboxylic acids with halogens to give organic halides. [Cläre Hunsdiecker, "et al." U.S. Patent # 2,176,181.] [Heinz Hunsdiecker; Cläre Hunsdiecker "Ber." 1942, "75", 291.DOI|10.1002/cber.19420750309 ] [Borodin, A. "Ann." 1861, "119", 121.DOI| 10.1002/jlac.18611190113 ] [Allen, C. F. H.; Wilson, C. V. "Organic Syntheses", Coll. Vol. 3, p.578 (1955); Vol. 26, p.52 (1946). ( [http://www.orgsyn.org/orgsyn/prep.asp?prep=cv3p0578 Article] )] The reaction is named after Heinz Hunsdiecker and Cläre Hunsdiecker.

Several reviews have been published.Johnson, R. G.; Ingham, R. K. "Chem. Rev." 1956, "56", 219. (Review)] [Wilson, C. V. "Org. React." 1957, "9", 341. (Review)]

Mercuric oxide will also effect this transformation. [Meek, J. S.; Osuga, D. T. "Organic Syntheses", Coll. Vol. 5, p.126 (1973); Vol. 43, p.9 (1963). ( [http://www.orgsyn.org/orgsyn/prep.asp?prep=cv5p0126 Article] )] [Lampman, G. M.; Aumiller, J. C. "Organic Syntheses", Coll. Vol. 6, p.179 (1988); Vol. 51, p.106 (1971). ( [http://www.orgsyn.org/orgsyn/prep.asp?prep=cv6p0179 Article] )]

Reaction mechanism

The reaction mechanism of the Hunsdiecker reaction is believed to involve organic radical intermediates. The silver salt of the carboxylic acid 1 will quickly react with bromine to form intermediate 2. Formation of the diradical pair 3 allows for radical decarboxylation to form the diradical pair 4, which will quickly recombine to form the desired organic halide 5.

Variations

imonini reaction

The reaction of silver salts of carboxylic acids with iodine is called the Simonini reaction , named after Angelo Simonini a student of Adolf Lieben at the University of Vienna. [cite journal
title = Über den Abbau der fetten Säuren zu kohlenstoffärmeren Alkoholen
author = Simonini, A.
journal = Monatshefte für Chemie
volume = 13
issue = 1
pages = 320–325
year = 1892
url =
doi = 10.1007/BF01523646 ] [cite journal
title = Über den Abbau der fetten Säuren zu kohlenstoffärmeren Alkoholen
author = Simonini, A.
journal = Monatshefte für Chemie
volume = 14
issue = 1
pages = 80–92
year = 1893
url =
doi = 10.1007/BF01517859 ]

References

ee also

*Barton-McCombie deoxygenation
*Kochi reaction


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